- Palladium-catalyzed cyclization of unsaturated β-amino alcohols: A new access to enantiopure bicyclic oxazolidines
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Image Presented Chiral unsaturated β-amino alcohols possessing a dialkylamino function cyclize in the presence of Pd(II) catalysts and reoxidants to afford enantiopure bicyclic oxazolidines with total regio- and stereocontrol. The scope and limitations of
- Alladoum, Jeanne,Vrancken, Emmanuel,Mangeney, Pierre,Roland, Sylvain,Kadouri-Puchot, Catherine
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scheme or table
p. 3746 - 3749
(2011/02/28)
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- Short enantioselective syntheses of trans-5-alkylprolines from new functionalized amino alcohols
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(Chemical Equation Presented) Amino alcohols, having an enol ether function, cyclized in acidic medium to give quantitatively diastereosomerically pure bicyclic compounds that were transformed in five steps in enantiopure trans-5-alkylproline derivatives.
- Alladoum, Jeanne,Roland, Sylvain,Vrancken, Emmanuel,Mangeney, Pierre,Kadouri-Puchot, Catherine
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experimental part
p. 9771 - 9774
(2009/04/06)
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- Asymmetric syntheses of 2-substituted and 2,5-disubstituted pyrrolidines from (3S,5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine
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Benzotriazole, 2,5-dimethoxytetrahydrofuran, and (S)-phenylglycinol in one step gave 80% of (3S, 5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl-[2,1- b]oxazolopyrrolidine (6), whose crystal structure was confirmed by X-ray crystallography. Novel chiral pyrrolidine synthon 6 reacts with organosilicon (allyltrimethylsilanes and vinyloxytrimethylsilanes), organophosphorus, organozinc, and Grignard reagents to afford chiral 2-substituted and 2,5- disubstituted pyrrolidines.
- Katritzky, Alan R.,Cui, Xi-Lin,Yang, Baozhen,Steel, Peter J.
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p. 1979 - 1985
(2007/10/03)
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- A short asymmetric synthesis of 2,5-disubstituted pyrrolidines
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A novel approach to chiral 2,5-disubstituted pyrrolidines, starting from chiral 2-phenyl-glycimol, 1,5-dimethoxytetrahydrofuran, and benzotriazole, involves the diastereoselective substitution by Grignard reagents of a benzotriazolyl group in a crystalline intermediate obtained in high yield.
- Katritzky, Alan R.,Cui, Xi-Lin,Yang, Baozhen,Steel, Peter J.
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p. 1697 - 1700
(2007/10/03)
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